


••Red’s My Color••

by grapefruitghostie



Series: SPN Pride Bingo 2020 [2]
Category: Supernatural
Genre: Bottom Dean Winchester, Boys In Love, Boys in Skirts, Crossdressing Dean Winchester, Intimacy, Lingerie, M/M, Making Love, Porn with Feelings, Romance, Sensuality
Language: English
Status: Completed
Published: 2020-06-09
Updated: 2020-06-09
Packaged: 2021-03-04 06:02:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,844
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24538939
Author URL: https://archiveofourown.org/users/grapefruitghostie/pseuds/grapefruitghostie
Summary: Spaces filled: crossdressing- Y’all remember in scoobynatural when Dean was wearing that STUPID red ascot? Okay, well red is his color.
Relationships: Castiel/Dean Winchester
Series: SPN Pride Bingo 2020 [2]
Series URL: https://archiveofourown.org/series/1773490
Kudos: 34





	••Red’s My Color••

**Author's Note:**

> Author? Writing destiel?! It took them long enough (‘:

Dean realized, looking at himself in the mirror, that he’d never felt more _alive_. His shaking hands ran over the plasticky straps of the red harness that covered his chest and his whole body flushed a matching shade. It laid like an inverted pentagram, exposing his nipples through two of the points and coming to a point right between his ribs. 

He wore a tight, white miniskirt that barely stretched over his ass, exposing the way that the lingerie harnessed his muscular thighs. Dean felt pretty like this. He just hoped that Castiel liked it as much as he did.   
  
They’d very briefly discussed how much Dean enjoyed wearing women’s clothing, but _this_ \- oh, this was a complete surprise. However, it was their anniversary, and Dean wanted to surprise his lover all the while indulging himself.

Dean Winchester reached for the door with a nervous hand and stepped out of their shared bedroom. Luckily they had the place to themselves for the weekend, but Dean still opted for a bathrobe as he searched for Cas.   
  


“Dean?” He heard Cas call out, “I’m in the kitchen.”

“Good morning, lover,” Dean hummed as he stepped into the kitchen. 

Castiel noticed that wild stare in his lover’s eye but said nothing. He just observed. Cas watched Dean saunter past the coffee pot and plop right down in his lap. Dean felt the short skirt ride up and expose him completely under the robe when he swung a leg over Cas’s to straddle him.

”Oh, good morning, baby,” Castiel grinned, kissing his neck lazily and resting his large hands on Dean’s thighs. He felt the straps on Dean’s thighs and instantly his curiosity was piqued.

“Can I see what you got on under there?” He pondered. 

Dean kissed him hungrily and slid off the bench seat. He adjusted the skirt so it was covering his now-hardening prick once more and, when he was ready, Dean slowly let the robe slide down his shoulders and pool around his bare feet on the floor.

”Just tell me if it’s weird and I can change, I know I di-“ 

Dean was cut off by Castiel rising to his feet, taking the two strides towards him, and pulling him into a dire kiss. He was holding Dean’s hips so tightly and drowning himself in the kiss. Dean had wrapped his arms around his angel’s neck and pressed up against him so that they were chest to chest. 

Castiel’s hands finally found Dean’s perfect ass and he lifted, the other hopping up to wrap his legs around pajama clad hips. They kissed like this all the way to the bedroom - one of Castiel’s hands supporting Dean’s weight and the other feeling around for walls or door frames. Once they arrived safely in their bedroom, Dean was dropped onto the mattress without celebration.   
  
“You’re perfect, Dean,” the angel husked, taking time to drink up the sight of Dean’s handiwork with the straps. 

“Well, I’m sure glad you like it,” Dean teased. 

“I love it,” Cas hummed before locking eyes with Dean, “I love _you_.”

”I love you too,” he replied, voice barely above a whisper. 

Castiel pulled his sleep shirt off and laid beside his human on the bed. He reached out and traced the pattern of the harness over his chest, watching in rapt focus as chill bumps rose on Deans scarred skin. He spent what felt like ages just admiring Dean, adoring him. Finally he kissed Dean’s jaw and neck, pulling soft sighs from the taller man’s lips. 

“Cas, please,” he hummed but Castiel shushed him.

”Shh, wait a minute,” the angel pleaded, “we don’t need to rush.”

Dean whined in false frustration. Truth be told, he lived for this mushy crap. Dean Winchester was a total pillow-princess, okay? He wanted soft touches and gentle reminders of how much he was loved and cared for. He wanted Cas to hold him and keep him down to Earth.   
  
While Dean had been daydreaming about Cas, said angel had tossed a leg over Dean’s waist and was fiddling with the zipper on the side of the skin-tight skirt.

“This doesn’t look very comfortable,” Castiel observed.

”It’s not,” Dean admitted. 

“Hips,” Cas instructed and the other immediately acted, lifting his hips off the mattress so that the skirt could be wrestled off, “can we keep this little red number though?”

Dean smiled widely and nodded, “please.”

Castiel hummed appreciatively and bent to kiss down Dean’s chest, stopping to pay some attention to his soft-pink nipples. Dean winced at the sudden stimulation but it turned to a moan quickly as his hand flew up to grasp Castiel’s soft hair. Castiel instinctively moaned at the tug on his hair, sending electricity clear through to Dean’s spine.

With his mouth on one nipple, Castiel busied his fingers by rubbing and pinching the other, making the most heavenly noised that spilled from Dean. Eventually though, Castiel grew bored of this and continued his trail of kisses and bites down Dean’s stomach. He could obviously see that Dean was hard as nails from his affections, but Castiel decided to ignore that for a moment. For now, however, Cas just sucked dark purple marks into the other's soft, freckle-specked hips.

Dean knew better than to beg; Cas wasn't going to budge. But he found that he didn't need to wait much longer because as soon as the thought crossed his mind, Cas was on him. Dean whined as the angel's soft lips wrapped around his throbbing prick. As soon as he was there, Cas was gone again - licking a tentative stripe up the underside of his thick cock and stopping to tease his leaking head. 

"Cas," Dean breathed, digging his nails into Castiel's biceps.

The angel didn't respond other than going down on him once more, moaning when he felt the blunt head of Dean's cock breach his throat. 

"Christ!" Dean yelped, bucking his hips instinctively at the feeling of his lover's tight throat. He silently thanked Chuck in that instant for not bothering to give angels any sort of gag reflex. He was only able to handle a few more moments of this heavenly torture before he felt that familiar coil winding in the pit of his stomach and he tugged Castiel away. 

"Are you okay?" he asked instinctively, "I didn't hurt you, did I?"

"Fuck, no Cas, are you kidding me? You're perfect," Dean reassured him, all the while trying to catch his breath, "I want you inside me, baby. Please."

Castiel hummed and lifted his hand to snap the remainder of his clothes away, but Dean reached up and held it instead. He locked eyes with his angel and sat up, tugging the thin pajama pants down. Once they were successfully pooled around his knees, Dean bent to mouth at his cock through his now-tight briefs. Cas moaned openly and only then did Dean pull them down, laying back on the bed and letting his lover chase him. 

"You're a tease," Castiel fake-complained.

He kicked the rest of his clothing off the edge of the bed and laid right on top of Dean, holding him tightly as they kissed more. Dean could feel Castiel rustling around in the bedside drawer and his body nearly vibrated in excitement. Cas drew back his hand with a bottle of lube and sat up to scoot down Dean's body. 

Unscrewing the cap, Castiel smiled at the sight in front of him. Dean's fat lips were parted in a shallow pant, and his eyes were wide with anticipation. Furthermore, his legs were spread open lewdly and his cock was nearly dripping from the stimulation. 

Cas couldn't make him wait any longer. He dribbled too much lube on his fingers and pulled Dean closer by the hips, reaching between his legs to tease an index against his hole before slipping it in. 

Dean whined unabashedly, pressing back for _more_. Castiel smiled at his lover's reaction and slid in a second finger, watching Dean fall apart below him. Sweetly, Castiel kissed the man's neck as he stretched him sensually slow. He waited for Dean's face to fall to know that he was ready for a third, watching it twist up again in pleasure as he crooked the three fingers up against his prostate. 

" _Fuck_ ," he breathed, "c'mon, I'm ready."

Castiel only hummed in response but didn't stop fingering him just yet, he wanted to hear Dean's whines just a moment longer. Finally, though, he pulled his fingers away, wiping the excess on his own straining cock. Dean's head was tossed back against the pillow and his eyes were shut in bliss as Cas pressed into him, pulling a long moan from both of their lips. 

He rearranged them so that Dean's muscular thighs were wrapped around his hips as he bottomed out and rested his head against Dean's shoulder. They stayed there for only a moment before Castiel sat up to begin his work. 

Noticing Dean's hands gripping the sheets, Cas reached for one and laced their fingers together sweetly while his other hand rested on the lingerie band on his hip. Profanities slipped from their mouths as Cas's perfect cock dragged against his prostate with every deliberate thrust. The air was heavy around them but neither minded. Though it was hard to breathe, they improvised - sharing one breath as their lips were hardly centimetres from one away another. It wasn't much longer before Castiel was getting close to the edge, and he could see by Dean's face that he wasn't alone. 

"Baby," he nearly whispered, "I'm close. Come with me?"

Dean nodded excitedly, gazing up at his angel with needy green eyes. Castiel smiled fondly and caught his lips in a tender kiss, moving his hand from Dean's hip to his prick, tugging him off and thumbing at his slit. Somehow they actually managed to come at the same time, which had never happened before. It was usually more abstract, but today Dean howled as he spilled all over Castiel's fingers and his own stomach at the same moment that Cas grunted into his ear and finished inside his tight walls. 

Cas collapsed immediately, still inside of Dean as he tried to catch his breath. Once the position grew uncomfortable, he slid out of Dean who shuttered at the loss. 

"I love you," He mumbled and Dean just chuckled. 

"I love you too," Dean said as he kissed the angel's messy hair, "happy anniversary, baby."

"Happy anniversary."

They just laid there in content silence for a moment, Castiel tracing shapes on Dean's chest and Dean twirling his lovers dark brown hair in his fingers. Eventually Dean convinced him to shower and they did. It took the both of them to wrangle Dean out of the plasticky harness that was now chaffing him from the sweat and cum.

They laughed together about that, then proceeded to shower together and make lunch together and go for a drive together. It was Dean's favorite anniversary to date - and Castiel's, but he wouldn't admit to having a favorite. 

**Author's Note:**

> That probably sucked, Author hasn’t written anything this softcore in a loooong time


End file.
